Diethyl (aminomethyl)phosphonate → HCID 20229893, compound

HRID 2290680Notes

Reaction equation

HRID 2290680 reaction equation
[NH2:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].[F:11][C:12]([F:33])([F:32])[C:13]1[CH:14]=[CH:15][C:16]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22]([N+]([O-])=O)[CH:21]=2)=[N:17][CH:18]=1>C1(C)C=CC=CC=1>[N+:26]([C:23]1[CH:22]=[CH:21][C:20]([O:19][C:16]2[CH:15]=[CH:14][C:13]([C:12]([F:33])([F:11])[F:32])=[CH:18][N:17]=2)=[CH:25][C:24]=1[NH:1][CH2:2][P:3](=[O:10])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6])([O-:28])=[O:27]

Participants

4

Reactant 2

HCID 1596920Diethyl (aminomethyl)phosphonateHCID 202299032-(3,4-Dinitrophenoxy)-5-(trifluoromethyl)pyridine

Product 1

HCID 20229893HCID 20229893, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

With stirring, 7.6 g (0.045 mole) of diethyl aminomethylphosphonate are added dropwise to a solution of 15 g (0.045 mole) of (5-trifluoromethyl-2-pyridyloxy)-3,4-dinitrobenzene in 50 ml of toluene, and the mixture is heated for 12 hours to reflux. The mixture is then concentrated and the residue is chromatographed over silica gel with a 1:4 mixture of hexane/ethyl acetate, affording 9.8 g (48.7% of theory) of the title compound with a melting point of 74°-76° C.

Workup

  1. temperaturethe mixture is heated for 12 hours
  2. temperatureto reflux
  3. concentrationThe mixture is then concentrated
  4. customthe residue is chromatographed over silica gel with a 1:4 mixture of hexane/ethyl acetate

Sources & evidence

ORD record
ord-f12330553e9349cc852dc3c5d242daf7
Source dataset
uspto-grants-1986_10
Patent number
US04618358

Reaction notes

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